Trifluoroacetic acid → HCID 86721881, compound

HRID 1049031Notes

Reaction equation

HRID 1049031 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:36])(=[O:35])[N:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:17][CH:16]=2)[C@H:10]([OH:37])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:21]([C:18]2[CH:17]=[CH:16][C:15]([O:14][C@@H:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]3[OH:37])=[CH:20][CH:19]=2)(=[O:36])=[O:35])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86721880HCID 86721880, compound

Product 1

HCID 86721881HCID 86721881, compoundYield 111.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)trans-4-{4-[(4-chloro-benzyl)-isobutyl-sulfamoyl]-phenoxy}-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (222 mg, 402 μmol) in DCM (8 mL) was added TFA (2 mL) and the reaction was stirred at room temperature for 30 minutes. The reaction was concentrated and purified by SCX column eluting with 2 M NH3 in MeOH to give N-(4-chloro-benzyl)-4-((+/−)trans-3-hydroxy-piperidin-4-yloxy)-N-isobutyl-benzenesulfonamide (202 mg, 447 μmol). LCMS (m/z, Method A) ES+ 453 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by SCX column
  3. washeluting with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-854d0a499f1645db9493055a1d181422
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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